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How do you feel if someone who is not medium attractive winks at you?
Or if they just say something weird, like a joke you don't appreciate, and wink at you?
I guess there has to be some kind of established not-a-creepy-stranger before risking a wink becomes appropriate.
Physically unattractive, but a good wink would still pique my interest, but it's never happened to me. Winking is kind of rare. It's like proof that they're fast, clever, and confident, and that they desire a rapport with me.
Yes, the wink has to be paired with something clever, or wise, or nice. Some kind of friendly banter. You'd have to be already attractive to wink out of the blue, but if you're already attractive and you wink, I'd probably like that too. It's conveying interest. It's conspiratorial and playful.